Triethylamine → HCID 18536628, compound

HRID 412048Notes

Reaction equation

HRID 412048 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=O)[CH:5]=[CH:6][CH:7]=1.[C:12]([N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1)([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].CC[N:27](CC)CC.O=C1N(P(Cl)(N2CCOC2=O)=O)CCO1>C(Cl)Cl.C(Cl)Cl.CO>[C:15]([O:14][C:12]([N:19]1[CH2:20][CH2:21][N:22]([CH:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([OH:1])[CH:3]=2)[C:9]([NH2:27])=[O:11])[CH2:23][CH2:24]1)=[O:13])([CH3:18])([CH3:17])[CH3:16]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 121223'-Hydroxyphenylacetic acidHCID 143452tert-Butyl piperazine-1-carboxylateHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chloride

Product 1

HCID 18536628HCID 18536628, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 21226129Dichloromethane methanolSolvent

Procedure

3-Hydroxyphenylacetic acid (0.50 g, 3.3 mmol), BOC piperazine (0.737 g, 3.96 mmol), Et3N (0.92 mL, 6.6 mmol), and CH2Cl2 (7 mL) were combined, cooled to 4° and solid Bis(2-oxo-3-oxazolidinyl)-phosphinic chloride (0.840 g, 3.3 mmol)was added under Ar. The ice bath was removed and a clear solution was obtained on warming to 23°. After 1 hour tlc (silica plates, 19:1 CH2Cl2/CH3OH) indicated a completed reaction. The reaction was diluted with CH2Cl2(100 mL), washed with 0.3 N HCl (20 mL), H2O (20 mL), satd aq NaHCO3 (20 mL) and Satd aq NaCl (20 mL), dried (Na2SO4) filtered and the filtrate was diluted with CH3OH til ca 4% CH3OH in CH2Cl2 and filtered through a pad of silica to afford the title compound as a white foam. 1H NMR (CDCl3): d 7.13 (m, 1), 6.81 (s, 1), 6.73 (d, 1), 6.68 (d, 1), 3.69 (s, 2), 3.59 (m,2), 3.39 (m, 4), 3.22 (m, 2), 1.46 (s, 9).

Workup

  1. temperaturecooled to 4°
  2. customThe ice bath was removed
  3. customa clear solution was obtained
  4. temperatureon warming to 23°
  5. customa completed reaction
  6. washwashed with 0.3 N HCl (20 mL), H2O (20 mL)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. additionthe filtrate was diluted with CH3OH til ca 4% CH3OH in CH2Cl2
  10. filtrationfiltered through a pad of silica

Sources & evidence

ORD record
ord-09702f379750461290b80df62cc2e70d
Source dataset
uspto-grants-2003_05
Patent number
US06562832B1

Reaction notes

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